1116-77-4|4,4-Diethoxy-N,N-dimethyl-1-butanamine| Ambeed

Structure of 1116-77-4

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Quality Control of [ 1116-77-4 ] Purity: 97% SDS Specification

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Product Details of [ 1116-77-4 ]

CAS No. :	1116-77-4
Formula :	C₁₀H₂₃NO₂
M.W :	189.30
SMILES Code :	CN(C)CCCC(OCC)OCC
MDL No. :	MFCD00671479
InChI Key :	QKXMWBLNSPNBEY-UHFFFAOYSA-N
Pubchem ID :	547078

Safety of [ 1116-77-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Application In Synthesis of [ 1116-77-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1116-77-4 ]

[ 1116-77-4 ] Synthesis Path-Downstream 1~25

1
[ 1116-78-5 ]
[ 1116-77-4 ]

References: [1]Croatica Chemica Acta,1964,vol. 36,p. 103,106.

2
[ 1116-77-4 ]
[ 5929-14-6 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1965,vol. 1,p. 2011 - 2014.
Zhurnal Organicheskoi Khimii,1965,vol. 1,p. 1973 - 1976.

3
[ 19070-16-7 ]
[ 122-51-0 ]
[ 1116-77-4 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1965,vol. 1,p. 2011 - 2014.
Zhurnal Organicheskoi Khimii,1965,vol. 1,p. 1973 - 1976.

4
[ 50-00-0 ]
[ 6346-09-4 ]
[ 1116-77-4 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 2401 - 2404.

5
[ 1116-77-4 ]
[ 104459-70-3 ]
2-Hydroxy-1,1-dimethyl-pyrrolidinium [ No CAS ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 3738 - 3741.

7
[ 64-17-5 ]
hydrochloride of γ-dimethylamino-butyraldehyde [ No CAS ]
[ 1116-77-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1915,vol. 410,p. 63.

8
[ 6346-09-4 ]
[ 1116-77-4 ]

References: [1]Croatica Chemica Acta,1964,vol. 36,p. 103,106.

9
[ 1116-77-4 ]
C₁₆H₃₆N₄O₂⁽²⁺⁾*2I^(1-) [ No CAS ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1965,vol. 1,p. 2011 - 2014.
Zhurnal Organicheskoi Khimii,1965,vol. 1,p. 1973 - 1976.

10
[ 1116-77-4 ]
C₁₈H₄₀N₄O₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1965,vol. 1,p. 2011 - 2014.
Zhurnal Organicheskoi Khimii,1965,vol. 1,p. 1973 - 1976.

11
[ 1116-77-4 ]
C₂₂H₄₈N₄O₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1965,vol. 1,p. 2011 - 2014.
Zhurnal Organicheskoi Khimii,1965,vol. 1,p. 1973 - 1976.

12
[ 109-54-6 ]
[ 122-51-0 ]
[ 1116-77-4 ]

Yield	Reaction Conditions	Operation in experiment
75.8%	With iodine; magnesium; In benzene; for 3.25 - 4.33333h;Heating / reflux;	Into a 2L four-necked round bottom flask was charged magnesium turnings (25gr) under nitrogen atmosphere. Benzene [(50ML),] the above benzene solution [(50ML),] triethyl orthoformate (20gr), and a small crystal of iodine were added to the reaction flask and slowly heated to reflux temperature. Within 15-20min of refluxing period, a vigorous reaction took place indicating the initiation of Grignard reaction. Remaining quantity of benzene solution and triethyl orthoformate of the [FORMULA-XVII] where [R3 = R5] = Et (174gr) were separately taken into two addition funnels and slowly added in 3-4hrs period to the reaction mixture under reflux temperature. The reaction mass was cooled to [25C] and filtered through celite pad. The cake was washed with benzene [(100ML).] Benzene was removed from the reaction mass using 20cm Vigroux column at atmospheric pressure. The residue was distilled under mild vaccum keeping mass temperature below [100C] to get the excess triethyl orthoformate (60gr). Finally, [4- (N,] N- dimethylamino)-butyraldehyde diethyl acetal was distilled under vaccum to get 125gr (75.8%) as colourless liquid. B. p.: [140-150C/15-20MM.]
72.8%	With iodine; magnesium; In cyclohexane; for 5.25 - 6.33333h;Heating / reflux;	Into a 2L four-necked round bottom flask was charged magnesium turnings (25gr), cyclohexane [(50ML),] the above cyclohexane solution [(50ML),] triethyl orthoformate (20gr), and a small crystal of iodine were added into the flask and heated to reflux temperature. Within [15-20MIN] of reflux, vigorous reaction took place indicating the initiation of Grignard reaction. Remaining quantity of the cyclohexane solution [(600ML)] and triethyl orthoformate of the [FORMULA-XVII] where R3 = [R5] = Et (175gr) were taken into two separate addition funnels and added to the reaction mass at reflux temperature over a period of [3-4] hrs. After the addition, the reaction mass was maintained at reflux for another 2hrs and cooled to [25C.] The reaction mass was filtered over a celite pad and washed the cake with 100ml of cyclohexane. Cyclohexane was removed from the reaction mass by ordinary distillation keeping a 20cm vigroux column. Excess triethyl orthoformate was distilled under mild vaccum keeping the mass below [80C.] Finally, the residue was distilled under vaccum to afford 120gr (72.8%) of 4- (N, N- dimethylamino) butyraldehyde diethyl acetal as a colorless liquid.
	With magnesium; In cyclohexane; at 65 - 70℃; for 6h;	100GMS (0. 66MOL) of chloro bromo propane was taken in 100ML of cyclohexane and 125gms of 42% caustic soda lye was added at 20-25C. The mass was stirred for 60min at 25-30 C and LOOGMS of 40% DIMETHYLAMINE was added. The mass was stirred for 24 hours at 25-30 C and 200ML of cyclohexane was added. The organic layer was separated and dried with sodium sulfate. The organic layer was used for next stage without ISOLATION/PURIFICATION. 20 gms of magnesium turnings was taken the flask and 80ML of TRIETHYLORTHO formate was taken in a well-dried flask which was equipped with an addition funnel, thermometer socket and reflux condenser. The reaction mass was heated to 65-70C and the above organic layer was added in 4 hours. The reaction mixture was stirred for 2 hours at G5-70 C and cooled to 25-30C, The mass was filtered and filtrate was stripped off solvent under reduced pressure. The product was distilled under 1 OMM/HG at 135-140 C to get 30gms of the >94% PURE (GC) 4, 4-DIMETHYLAMINO butyraldehyde dimethyl acetal, which can be used straight away for the next stage

References: [1]Patent: WO2003/101931,2003,A2 .Location in patent: Page 14-15.
[2]Patent: WO2003/101931,2003,A2 .Location in patent: Page 15-16.
[3]Patent: WO2004/99141,2004,A1 .Location in patent: Page 9-10.

13
[ 1116-77-4 ]
(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride [ No CAS ]
[ 139264-17-8 ]

Yield	Reaction Conditions	Operation in experiment
62 g	With hydrogenchloride; In water;Reflux;	Example 2 Synthesis of Zolmitriptan (I) Conc. hydrochloric acid (200 ml) was added to (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride (100 gms) in water (650 ml) and treated with N,N-dimethylamino butyraldehyde diethyl acetal (95 gms). The reaction mixture was warmed and upon completion of the reaction, as monitored by HPLC; the pH was adjusted in the range of 7.0 to 8.0 using aq. ammonia followed by extraction with ethyl acetate. The organic layer was separated and aqueous layer was made alkaline between pH 8.0 to 12.0 using aq. ammonia and extracted with dichloromethane (750 ml). The organic layer was separated and concentrated to give a residue which was diluted with ethyl acetate (200 ml). The organic layer was concentrated, cooled and filtered to yield pure Zolmitriptan (I). Yield: 62 gms Purity (HPLC)?99.7%

References: [1]Patent: EP1227095,2002,A2 .Location in patent: Example 1.
[2]Patent: US2014/228582,2014,A1 .Location in patent: Paragraph 0031-0032.
[3]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E332-E334.

14
[ 1116-77-4 ]
(4-[1,2,4]triazol-1-ylmethylphenyl)hydrazine hydrochloride [ No CAS ]
[ 1016900-24-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 20 - 25℃; for 1h;	Example-2: Preparation of Rizatriptan Benzoate:- l-(4-Hydrazinophenyl)methyl-l52:,4-triazole hydrochloride (7.0 kg.) in Cone. HCl (35.0 It.) is stirred for 30 min at 20-250C, to that water (140.0 It.) is added and stirred for another 30min at 20-250C. 4-(Dimethylamino) butanal diethylacetal (7.10 kg.) is added slowly at 20-250C and stirred for 60 min. The reaction mixture is hated to 70-750C and maintained for 60 min. After completion of reaction, cooled the mass to 3O0C, adjusted the pH to 6.0-6.5 and extracted with methylene chloride (2 x 35 It.). Aq.layer is separated and adjusted the pH to 10-11 and extracted with ethyl acetate (3 x 55 It.). Ethyl acetate is removed under vacuum and the residue is chromatographed on silica gel (55 kg.) and eluted with ethyl acetate (25 It.) followed by methanol (30 It.) to give Rizatriptan as residue. The obtained residue is dissolved in ethanol (15 It.) and pH is adjusted to 6.0- 6.5 with benzoic acid (1.8 kg.) in ethanol (3.5 It ) at 30-350C. The reaction mass is cooled to O0C and stirred for lhr. The product is centrifuged and washed with ethanol ( 3 It) to yield Rizatriptan benzoate (3.0 kg.) with purity >99.0%.

References: [1]Patent: WO2007/54979,2007,A1 .Location in patent: Page/Page column 5; 9.

15
[ 1116-77-4 ]
[ 1034806-43-3 ]
[ 144034-80-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2Preparation of N,N-dimethyl-5-(lH-l,2,4-triazol-l-ylmethyl)-lH-indoIe-3- ethanamine benzoateA mixture of 4-(lH-l,2,4-triazol-lylmethyl)phenylhydrazinesulfonic acid (50 g, 0.186 mol) and 4-(dimethylamino)butanal diethyl acetal (45.70 g, 0.242 mol) was stirred in 15 % w/w aqueous sulfuric acid (500 ml) at 35-4O0C for 9 h. The reaction mixture was then cooled to 0-50C and pH was adjusted to 10.5-11.0 using aqueous sodium hydroxide solution. The product was extracted with ethyl acetate and the solvent was removed by distillation under reduced pressure to obtain the Rizatriptan base as an oily mass. The Rizatriptan base was dissolved in acetone (200 ml) and stirred with benzoic acid (22.69 g, 0.186 mol) at 0-50C for 3 h. The solid precipitated was filtered and stirred in a mixture of ethanol (50 ml) and acetone (25 ml) at 60-650C for 1 h. The resulting slurry was cooled to 5-1O0C and filtered to obtain crude Rizatriptan benzoate product. This crude Rizatriptan benzoate was crystallized from ethanol to obtain pure Rizatriptan benzoate. YIELD: 16 g (HPLC PURITY: >99.6%); Example 3Preparation of N,N-dimethyl-5-(lH-l,2,4-triazol-l-ylmethyl)-lH-indole-3- ethanamine benzoateA mixture of 4-(lH-l,2,4-triazol-lylmethyl)phenylhydrazinesulfonic acid (50 g, 0.186 mol) and 4-(dimethylamino)butanal diethyl acetal (45.70 g, 0.242 mol) was stirred in 15 % w/w aqueous sulfuric acid (500 ml) at 38-420C for 9 h. The reaction mixture was then cooled to 0-50C and pH was adjusted to 10.5-11.0 using aqueous sodium hydroxide solution. The product was extracted with ethyl acetate and the solvent was removed by distillation under reduced pressure to obtain the Rizatriptan base as an oily mass. The Rizatriptan base was dissolved in acetone (200 ml) and stirred with benzoic acid (22.69 g, 0.186 mol) at 0-50C for 3 h. The solid precipitated was filtered and stirred in a mixture of ethanol (50 ml) and acetone (25 ml) at 60-650C for 1 h. The resulting slurry was cooled to 5-1O0C and filtered to obtain crude Rizatriptan benzoate product. This crude Rizatriptan benzoate was crystallized from ethanol to obtain pure Rizatriptan benzoate. YIELD: 16 g (HPLC PURITY: >99.6%)

References: [1]Patent: WO2008/75163,2008,A2 .Location in patent: Page/Page column 11-12.

16
[ 1116-77-4 ]
[ 152305-23-2 ]
[ 139264-17-8 ]

Yield	Reaction Conditions	Operation in experiment
		2.4 litres of concentrated HCl are added to 7.0 litres of water in a duplicator. In such diluted HCl 1.75 kg of (<S)-4-(4-aminobenzyl)-l,3-oxazolidine-2-one of formula (I) is stirred up and the mixture is cooled down to 0C under stirring. During the cooling an aqueous solution ofNaNO2 (0.64 kg NaNO2 / 1.4 litres of water) is prepared for diazotation. At the temperature of ca. O0C a solution OfNaNO2 / H2O is slowly added to the solution of the starting substance (I) on intensive stirring and cooling. After adding of all the nitrite the mixture is further stirred at ca. O0C for ca. 30 min. Example 2 - Reduction of the diazonium saltWeighed 0.28 kg of NaOH is dissolved in 7.0 litres of water and of 2.66 kg of sodium disulphite are added under stirring. After dissolution the mixture is cooled to ca. 20C. The diazonium salt solution is slowly added to the cooled disulphite solution under intensive stirring at the temperature of 2 - 5C. The mixture is then stirred at ca. 5C for additional 30 minutes. Then, it is heated up to ca. 25C and stirred at this temperature for 45 minutes.Further it is heated under a reflux condenser to ca. 6O0C while being stirred. After heating 900 ml of concentrated HCl is added to the reaction mixture and the mixture is stirred under the reflux condenser for another 5 hours. Then the mixture is diluted with 14 litres of water. <n="7"/>Example 3 - Fischer indole reactionThe diluted reaction mixture is heated up to ca. 90C. 1.75 kg of 4,4-diethoxy-N,N- dimethylbutylamine of formula II is weighed. The weighed acetal (II) is added to the reaction mixture, which is then brought to moderate reflux (at ca. 980C) and being stirred under the reflux condenser it is left to react for about 2.5 hours. After 2.5 hours from the start of the reflux the heating of the mixture is switched off and the reaction mixture is cooled to the laboratory temperature.Example 4 - Isolation of the raw toluene solvate of ZOLMITRIPTANAt the laboratory temperature and being stirred the cooled mixture is neutralized with a ca. 20% aqueous solution of NaOH. About 4 litres of toluene is added and the mixture is stirred to make an emulsion. Then, an aqueous solution of NaOH is slowly added under stirring until pH of ca. 9.5 is achieved. After approx. 30 minutes of stirring the solid product is filtered off and washed with water. It is dried at temperatures of about 300C to the constant weight (about 10 hours).
		Sodium nitrite (16 gm) in water (120 ml) was added slowly for a period of 30 minutes at 0 deg C to a solution of (S)-4-(4-Aminobenzyl)-2-oxazolidinone (40 gm), concentrated hydrochloric acid (46 ml) and water (480 ml) in round bottomed flask, cooled to 0 deg C and stirred for 1 hour. The above diazotized solution was added for a period of 30 minutes at 0 deg C to sodium sulfite (78.3 gm) in water (200 ml) in another round bottomed flask, cooled to 0 deg C, slowly allowed to room temperature, heated to 55 deg C and stirred for 15 minutes at 60 deg C. Added concentrated hydrochloric acid (80 ml) to the reaction mass, stirred for 16 hours at 60 deg C, nitrogen gas was applied and heated to 90 deg C. Water (80 ml) was added to the reaction mass for 15 minutes at 90 deg C, added 4-(dimethylamino)-butyraldehyde diethylacetal for a period of 40 minutes, heated to reflux, stirred for 3 hours at reflux, cooled to 25 - 30 deg C and the pH was adjusted to 7 by adding sodium hydroxide solution(30%, 230 ml). Extracted with ethyl acetate (7 X 200 ml), adjusted the pH of the aqueous layer to 10 by adding sodium hydroxide solution (30%, 100 ml), heated to 50 deg C and again extracted with ethyl acetate (8 X 200 ml) at 50 deg C. Both the organic layers were combined, dried with sodium sulfate, given carbon treatment and the solvent was distilled off completely under vacuum at 50 - 55 deg C, ethyl acetate (80 ml) was added to the reaction mass at 25 deg C, stirred for 1 hour and cooled to 10 deg C. Stirred for 30 minutes at 10 deg C, filtered the material and washed with chilled ethylacetate(20 ml) under nitrogen atmosphere and dried at 45 -50 deg C to yield 40 gm of (4S)-4-[[3-[2-(Dimethylamino)ethyl]~ 1 H-indol-5-yl]methyl]-2-oxazolidinone.(4S)-4-[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl]-2-oxazolidinone (40 gm, Zolmitriptan) was dissolved in isopropanol (200 ml) at 25 deg C, heated to reflux, stirred for 40 minutes at reflux and slowly allowed to cool to 0 deg C. Stirred the reaction mass for 1 hour at 0 deg C, filtered the compound, washed with chilled isopropanol(40 ml) and dried at 40 - 45 deg C under vacuum to yield (4S)-4-[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl]-2-oxazolidinone isopropanol solvate (32 gm, Zolmitriptan isopropanol solvate; HPLC purity. 99.32%). Zolmitriptan isopropanol solvate obtained above (32 gm) was dissolved in isopropyl acetate (2250 ml) at 25 deg C. Then the contents were heated to reflux and maintained for 30 minutes to form clear solution. The solution was cooled to 25 deg C during a period of 1 hour. The separated solid was filtered, washed with isopropyl acetate (160 ml) to obtain 32 gm of zolmitriptan isopropyl acetate solvate (HPLC purity: 99.8%).
		Example - 1;The preparation of (SV4-[(3-[2-(DimethgammalaminokthyIl-lH-indol-5-gammal1methvn-2- oxazolidinone (I):Charge to the flask 300 ml of cone, hydrochloric acid, 3L of demineralised water and 250 gms of (S)-4-(4-arninobenzyl)-2-oxazolidinone. Cool the reactor contents to between 0-5 DEG C and add aqueous sodium nitrite solution (99 gms in 900ml water), maintaining the temperature below 5 DEG C. After stirring for about 30 minutes add the diazonium salt solution to a chilled aqueous solution of sodium sulphite (492 gms in 800 ml water) maintaining the temperature below 10 DEG C. After stirring for 15 minutes slowly heat the resulting mixture to about 55-60 DEG C, and then slowly add 50 ml of cone. hydrochloric acid. The solution is maintained at about 60 DEG C for about 18 hours. Dilute the reaction mixture with 5L of water and heat to about 90 DEG C. Under a nitrogen atmosphere slowly add 246 gms of 4,4-diethoxy-N, N-dimethylbutylamine and heat at reflux for about 3 hours. Cool, and adjust the mixture to about pH7 using sodium hydroxide solution. Extract with chloroform and then adjust the aqueous layer to about pHIO, again using sodium hydroxide solution. Extract the product using chloroform. Treat the combined chloroform extracts (containing the product) with decolorizing charcoal, and filter through filter aid. Distil off most of the solvent and chill the suspension to about 0 DEG C. Centrifuge the crude product, wash with chloroform and vacuum dry at 50 DEG C. (150 gms, pale yellow powder, 99.4% HPLC purity)

References: [1]Patent: WO2008/104134,2008,A2 .Location in patent: Page/Page column title page; 5-7.
[2]Patent: WO2010/73256,2010,A2 .Location in patent: Page/Page column 4.
[3]Patent: WO2008/7390,2008,A2 .Location in patent: Page/Page column 6.

17
[ 1116-77-4 ]
[ 187975-62-8 ]
[ 139264-17-8 ]

Yield	Reaction Conditions	Operation in experiment
	at 90 - 98℃; for 2.5h;Heating / reflux;Product distribution / selectivity;	The diluted reaction mixture containing (S)-4-(4-hydrazmobenzyl)-1,3-oxazolidin-2-one prepared by diazotation 1.75 kg of the amine (I) and reduction in accordance with the above mentioned scheme is heated up to ca. 90C. 1.75 kg of <strong>[1116-77-4]4,4-diethoxy-N,N-dimethylbutylamine</strong> of formula II is weighed. The weighed acetal (II) is added to the reaction mixture, which is then brought to moderate reflux at ca. 980C and left to react being stirred under a reflux condenser for 2.5 hours. After 2.5 hours from the start of the reflux the heating of the mixture is switched off and the reaction mixture is cooled to the laboratory temperature.

References: [1]Patent: WO2008/104135,2008,A1 .Location in patent: Page/Page column 4.

18
[ 1116-77-4 ]
[ 144035-22-3 ]
[ 144034-80-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 3Reaction of 4-(1,2,4-triazol-1-yl-methyl)phenyl-hydrazine (IV) with 4-N,N-dimethylamino-butyraldehyde diethyl acetal (X) (Fischer indole synthesis)To the aqueous hydrazine (IV) solution obtained in example 2, conc. sulfuric acid (4.371) was added and the temperature of the reaction mixture was maintained for 2 hours at 65-70 C. After cooling to 20-25 C., 4-N,N-dimethylamino-butyraldehyde diethyl acetal (X) (3.15 kg) was added. The reaction was heated to 70 C. and maintained for 3-4 hours. After completion of the reaction, the reaction mixture was allowed to cool to 15-20 C. To this mixture, 25% aq. ammonia (7.251) was added to adjust the pH to 8.5-9. The solution was extracted with ethyl acetate (4×12.251). A solution of succinic acid (2.45 kg) in water (301) was added to the ethyl acetate extract. The mixture was stirred for 15 minutes. The aqueous layer was separated and washed with ethyl acetate (2×51). The aqueous layer was basified with 20% aq. NaOH to adjust the pH to 8.5-9. The solution was extracted with ethyl acetate (4 x 51). The combined ethyl acetate extracts were concentrated to give rizatriptan free base (VII) as oil (2.8 kg, 75.5% from 4-(1,2,4-triazol-1-yl-methyl)phenylamine (II)). Purity =99.7-99.9% (as measured by HPLC).
		Example 3: Reaction of 4-(1.2.4-triazol-l-yl-methyl)phenyl-hydrazine (IV) with 4-N.N- dimethylamino-butyraldehyde diethyl acetal (X) (Fischer indole synthesis); To the aqueous hydrazine (IV) solution obtained in example 2, cone, sulfuric acid (4.371) was added and the temperature of the reaction mixture was maintained for 2 hours at 65- 700C. After cooling to 20-250C, 4-N,N-dimethylamino-butyraldehyde diethyl acetal (X) (3.15kg) was added. The reaction was heated to 700C and maintained for 3-4 hours. After completion of the reaction, the reaction mixture was allowed to cool to 15-200C. To this mixture, 25% aq. ammonia (7.251) was added to adjust the pH to 8.5-9. The solution was extracted with ethyl acetate (4 x 12.251). A solution of succinic acid (2.45kg) in water (301) was added to the ethyl acetate extract. The mixture was stirred for 15 minutes. The aqueous layer was separated and washed with ethyl acetate (2 x 51). The aqueous layer was basified with 20% aq. NaOH to adjust the pH to 8.5-9. The solution was extracted with ethyl acetate (4 x 51). The combined ethyl acetate extracts were concentrated to give rizatriptan free base (VII) as oil (2.8kg, 75.5% from 4-(l,2,4-triazol-l-yl- methyl)phenylamine (IT)). Purity = 99.7-99.9% (as measured by HPLC).

References: [1]Patent: US2010/256208,2010,A1 .Location in patent: Page/Page column 6-7.
[2]Patent: WO2008/149152,2008,A1 .Location in patent: Page/Page column 13.

19
[ 14444-77-0 ]
[ 109-54-6 ]
[ 1116-77-4 ]

Yield	Reaction Conditions	Operation in experiment
72.7%		Into a 2L three-necked round bottom flask was added magnesium turnings (25gr) under nitrogen atmosphere and [50ML] of the above benzene solution added to the reaction flask. After adding a small crystal of iodine, reaction mass was heated to reflux temperature. After maintaining for 15 min, reaction got initiated and to the reaction mass remaining quantity of benzene solution was added slowly in 2-3hrs period. After the addition, reaction mass was maintained for lhr and a solution of phenyl diethyl orthoformate (171gr) in benzene [(200ML)] was added slowly over a period of lhr. After maintaining for 2hrs, reaction was cooled to [25C] and filtered on a celite pad. Solvent was removed from the reaction mass and the residue fractionally distilled to get 120gr (72.7%) [OF 4- (N,] N- dimethylamino) butyraldehyde diethyl acetal.

References: [1]Patent: WO2003/101931,2003,A2 .Location in patent: Page 19.

20
[ 1116-77-4 ]
4-Hydrazino-N-methylbenzenemethanesulphonamide hydrochloride [ No CAS ]
[ 103628-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 25 - 30℃; for 2h;Acidic aqueous solution;Product distribution / selectivity;	3 -(2-DimethylaminoVN-methyl- 1 H-indole-5 -methane sulphonamide benzoate A mixture of 100 gm of 4-hydrazino-N-methyl benzene methane sulphonamide hydrochloride, 1000 ml water, 82.5 gm 4-dimethylamino butyraldehyde diethyl acetal and 100 ml 2N HCl was taken and stirred for 2 hours at 25-30C. After reaction completion, reaction mass was basified with liquid ammonia and extracted with dichloromethane 750X2 ml. The dichloromethane layer and 700 gm polyphosphoric ester in 1500 ml dichloromethane was stirred at 35-400C for 2 hours and then 2 litres of water was added. The organic layer was separated and aqueous layer was basified with saturated sodium carbonate solution and the product was extracted with ethyl acetate. The organic layer was distilled off completely under vacuum and 500 ml acetone was added. Reaction mass was heated to reflux and 20.6 gm (0.169mol) of benzoic acid was added. After 2 hours of cooling at 0-5C,the crystal were filtered and dried to give 60-65 gm of 3 -(2-Dimethylamino)-N-methyl-l H-indole-5 -methane sulphonamide benzoate. 100 gm (0.239mol) of the above 3-(2-dimethylamino)-N-methyl-lH-indole-5- methane sulphonamide benzoate was taken in 500 ml methanol and stirred under reflux for 30 minutes. The methanol solution was treated with 10 gm charcoal and filtered and further cooled to 0-50C and filtered to give pure sumatriptan benzoate, of which the weight was 60-65 gm.100 gm of the pure benzoate salt was taken in water (1000 ml) and stirred. Simultaneously liquid was added slowly to obtain a pH of 9.0-9.5. The mixture was stirred for 1 hour and cooled to 0-50C. The cooled solution is further filtered, washed with water and sumatriptan base was collected and dried under vacuum at 40-450C. A mixture of 100 gm (0.398mol) of 4-Hydrazino-N-methyl benzene methane sulphonamide hydrochloride, 1000 ml water, 82.5 gm (0.436mol) 4 -dimethylamino butyraldehyde diethyl acetal and 100 ml 2N HCl was taken and stirred for 2 hrs at 25- 3O0C. After reaction completion basified with Hq. ammonia and extracted with dichloromethane 750X2 ml.The dichloromethane layer and 700 gm polyphosphoric ester in 1500ml dichloromethane was stirred at 35-4O0C for 2 hours and then 2 litres of water was added. The organic layer was separated and aqueous layer was basified with saturated sodium carbonate solution and the product was extracted with ethyl acetate. The organic layer was distilled off completely under vacuum and 200 ml methyl isobutylketone was added. After 2 hours of cooling at 10-15C, the crystal were filtered and dried to give 40-45 gm of 3-(2-Dimethylamino)-N-methyl-lH-indole-5~ methane sulphonamide

References: [1]Patent: WO2009/37718,2009,A2 .Location in patent: Page/Page column 10-11; 12-13.

21
[ 1116-77-4 ]
[ 622-88-8 ]
[ 17274-65-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2Preparation of 2-(5-bromo-1H-indol-3-yl)-N,N-dimethylethanamine (IV) 8.3 g of 4-dimethylaminobutanal diethylacetal (Tech grade from Aldrich) was added to a solution of 11.3 g of the product from Example 1 in a mixture of acetic acid (110 mL) and water (5 mL) and the resulting mixture was refluxed for 4 h. The mixture was cooled and evaporated in vacuum. The residue was dissolved in 100 mL of water and the pH was adjusted to 89 by saturated sodium bicarbonate, then extracted with 5×50 mL of dichloromethane. The combined organics were concentrated in vacuo and the residue was eluted through a silica column using DCM/EtOH/NH4OH (30:8:1) as eluant to give 3.0 g of the desired product as a pale yellow oil.1H NMR (DMSO-d6, delta): 2.53 (s, 6H, NMe2), 2.93 (s, 4H, CH2CH2), 7.16 (d, 1H, Ar), 7.26 (s, 1H, Ar), 7.33 (d, 1H, Ar), 7.75 (s, 1H, Ar), 11.20 (s, 1H, NH).

References: [1]Patent: US2010/217013,2010,A1 .Location in patent: Page/Page column 6-7.

22
[ 1116-77-4 ]
[ 119192-10-8 ]
[ 144034-80-0 ]

Yield	Reaction Conditions	Operation in experiment
		(ii) Preparation of crude rizatriptan benzoate; Into a clean IOOL glass reactor were charged water (20L) cone. HCl (8.5L), and l-(4- aminophenylmethyl)-l,2,4-triazole (5.0Kg). The reaction mass was stirred for 20-30min at 25-30 C and cooled to 0-5 C. Aqueous sodium nitrite (2.1Kg in 3.0Lof water) was added to the reaction mass below 5C over a period of 2hr. The reaction mass was maintained below 50C for lhr.Into a clean, 200L glass reactor were charged water (30 L) and sodium sulfite (9.0 Kg) under nitrogen atmosphere at 25-30 C. The resulting solution was cooled to below 10 C. Above diazonium salt solution was added to the reaction mass in 20-30 min period keeping the temperature below 10 C. The reaction mass was slowly heated to 65-7O0C over a period of 2.5-3. Ohr. After maintaining at this temperature for 2hr sulfuric acid EPO <DP n="12"/>(7.2L) was added to the reaction mixture and continued the maintenance at same temperature for 2.0-2.5 hr. The reaction mass was cooled to reach 20-25 0C.4-Dimethylaminobutyraldehyde diethyl acetal (7.8 kg) was added to the reaction mass in 30-45min keeping the temperature at 25-30 C. The reaction mass was maintained at this temperature for 4-5hr. TLC of the reaction mass indicated the absence of starting material. The reaction mass was heated to 35-400C and maintained for lhr. Temperature of the reaction mass was further raised to 60-65C and maintained for 3.5hr. The reaction mass was cooled to 20-30C and adjusted the pH of reaction mass to 6.5-7.0 with ammonia solution. Ethyl acetate (15L) was added to the reaction mass and stirred for 15- 20min and separated the organic layer. Aqueous layer pH was adjusted to 8.5-9.0 with ammonia solution. Aqueous layer was extracted with ethyl acetate (3 x 35L). Combined ethyl acetate layer was treated with activated carbon (lkg) and distilled of solvent under reduced pressure to get 4.7kg crude rizatriptan base as oil.The above crude rizatriptan base was dissolved in 18L of acetone at 25-30 0C. Benzoic acid (2.1kg) was added to the reaction mass at 25-30 C. After stirring for 45-60min at 25-30 C the reaction mixture was cooled to below 0 C and maintained for 10-12hr. The reaction mass was allowed to reach 20-25 0C and maintained for 2.5hr- before filtration. The wet cake was washed with 3.5L of acetone. Drying at 50-60 C gave 3kg of rizatriptan benzoate.; Example 4; Preparation of rizatriptan benzoate; (i) Preparation of crude rizatriptan benzoate:; Into a clean IOOL glass reactor were charged water (30L)5 cone. HCl (15kg), and l-(4- aminophenylmethyl)-l,2,4-triazole (7.5Kg). The reaction mass was stirred for 20-30min at 25-30 0C and cooled to below 0 C. Aqueous sodium nitrite (3.2Kg in 5Lof water) was added to the reaction mass below 5C over a period of 2hr. The reaction mass was maintained below 5C for lhr.Into a clean, 200L glass reactor were charged water (45 L) and sodium sulfite (13.5 Kg) under nitrogen atmosphere at 25-30 C. The resulting solution was cooled to below 10 0C. The above prepared diazonium salt solution was added to the reaction mass in 20-30 min period keeping the temperature below 10 C. The reaction mass was slowly heated to 65-70C over a period of 2.5-3.Ohr. After maintaining at this temperature for 2hr sulfuric acid (19.8kg) was added to the reaction mixture and continued the maintenance at same temperature for 2.0-2.5 hr. The reaction mass was cooled to reach 20-25 0C.4-Dimethylaminobutyraldehyde diethyl acetal (11.7 kg) was added to the reaction mass in 30-45min keeping the temperature at 25-30 0C. The reaction mass was maintained at this temperature for 4-5hr. TLC of the reaction mass indicated the absence of starting material. The reaction mass was heated to 35-40C and maintained for lhr. Temperature of the reaction mass was further raised to 60-65C and maintained for 3.5hr. The reaction mass was cooled to 20-30C and adjusted the pH of reaction mass to 6.5-7.0 with ammonia solution. Ethyl acetate (15L) was added to the reaction mass and stirred for 15-20min and separated the organic layer. Aqueous layer pH was adjusted to 8.8-9.2 with ammonia solution. Aqueous layer was extracted with ethyl acetate (3 x 45L). Combined ethyl acetate layer was treated with activated carbon (1.5kg) and distilled of solvent under reduced pressure to get 7.5kg of crude rizatriptan base as oil. EPO <DP n="14"/>The above crude rizatriptan base was dissolved in 3OL of acetone at 25-30 0C. Benzoic acid (3.5kg) was added to the reaction mass at 25-30 C. After stirring for 45-60min at 25-30 C the reaction mixture was cooled to below 0 C and maintained for 10-12hr. The reaction mass was allowed to reach 20-25 C and maintained for 2.5hr before filtration. The wet cake was washed with 5L of acetone. Drying at 50-60 0C gave 4.5kg of rizatriptan benzoate.

References: [1]Patent: WO2006/137083,2006,A1 .Location in patent: Abstract.

23
[ 1116-77-4 ]
(6Z,9Z,29Z,32Z)-octatriaconta-6,9,29,32-tetraene-18,20-diol [ No CAS ]
[ 1427469-90-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	With pyridinium p-toluenesulfonate; In toluene; at 80℃; for 1h;	A solution of the diol (6Z,9Z,29Z,32Z)-octatriaconta-6,9,29,32-tetraene-18,20-diol (7) (500 mg, 0.89 mmol) and 4,4-Diethoxy-N,N-dimethyl-1-butanamine (301mL, 1.34 mmol) in toluene (10 mL) was treated with PPTS (671 mg, 2.67 mmol) and heated (80 C.). After stirring (1 h) the solution was poured into NaOH (5M aq.) and extracted with CH2Cl2. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was subjected to chromatography (100% EtOAc) to yield 3-(4-((8Z,11Z)-heptadeca-8,11-dien-1-yl)-6-((9Z,12Z)-octadeca-9,12-dien-1-yl)-1,3-dioxan-2-yl)-N,N-dimethylpropan-1-amine (9) (399 mg, 68%) as a colorless oil. Rf 0.5 (10% CH3OH-CH2Cl2); 1H NMR (400 MHz, CDCl3) 5.45-5.29 (m, 8H), 4.80-4.75 (m, 0.5H), 4.52 (t, 0.5H), 4.08-3.97 (m, 0.5H), 3.78-3.67 (m, 0.5H), 3.59-3.48 (m, 1H), 2.78 (app. t, 4H), 2.32-2.19 (m, 8H), 2.13-2.00 (m, 8H), 1.87-1.75 (m, 2H), 1.68-1.15 (m, 42H), 0.91 (t, 6H). FW 656.12, C44H81NO2.

References: [1]Patent: US2013/64894,2013,A1 .Location in patent: Paragraph 0424; 0425.

24
[ 1116-77-4 ]
[ 932-88-7 ]
4,4-diethoxy-N-methyl-N-(3-phenylprop-2-yn-1-yl)butan-1-amine [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 6046 - 6050.
Angew. Chem.,2015,vol. 127,p. 6144 - 6148,5.

25
[ 1116-77-4 ]
2-acetyloxy-4-methoxy-4′-bromomethyl-benzophenone [ No CAS ]
N-(4-(2-acetoxy-4-methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan-1-aminium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate; at 20℃;Inert atmosphere;	Example 9 (0448) Synthesis of N-(4-(2-acetoxy-4-methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan- 1 -aminium bromide (0449) In a N2 purged 20mL weighed glass vial with stir bar is added 1 .5g (0.004mol, 1 .0 eq) of AcO-Bzp-OMe-CH2-Br prepared in Example 7 and 8 mL ethyl acetate to give a clear solution on stirring for 20mins at RT. 2.06 g 4,4-Diethoxy-N,N-dimethyl-1 -butanamine (0450) (<strong>[1116-77-4]NNDMABADEA</strong>, from TCI-America) (0.01 mol, 2.5 eq) is slowly added to the reaction solution with stirring. A precipitate is soon formed and gradually thickenes with stirring over 30- 60minutes. The reaction mixture is stirred at RT overnight. The stirring is stopped and the mixture is allowed to stand for an hour. The mixture is filtered through a coarse filter frit at around 850mbar. The precipitate is washed five times with 10ml_ ethyl acetate. The precipitate is transferred into a 10OmL rb flask with about 18ml of Dl Water. The residual organics are removed under reduced pressure to give a clear solution. The solution is filtered through a Whatman1 (1 1 urn) filter paper to give a clear solution with neutral pH, that is frozen and lyophilized to give a off white solid which is confirmed to be N-(4-(2-acetoxy-4- methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan-1 -aminium bromide and is stored under dry N2 in desiccator.

References: [1]Patent: WO2017/93835,2017,A1 .Location in patent: Page/Page column 49; 50.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Heat of Combustion • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Nomenclature of Ethers • Petasis Reaction • Preparation of Amines • Preparation of Ethers • Reactions of Amines • Reactions of Ethers • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 1116-77-4 ]

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Ethers

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CAS No.: 1116-77-4

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